Octreotide acetate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100675

CAS#: 79517-01-4 (acetate)

Description: Octreotide is a synthetic long-acting cyclic octapeptide with pharmacologic properties mimicking those of the natural hormone somatostatin. Octreotide is a more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Similar to somatostatin, this agent also suppresses the luteinizing hormone response to gonadotropin-releasing hormone, decreases splanchnic blood flow, and inhibits the release of serotonin, gastrin, vasoactive intestinal peptide (VIP), secretin, motilin, pancreatic polypeptide, and thyroid stimulating hormone.


Price and Availability

Size
Price

10mg
USD 360
Size
Price

Size
Price

Octreotide acetate is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100675
Name: Octreotide acetate
CAS#: 79517-01-4 (acetate)
Chemical Formula: C55H76N10O15S2
Exact Mass:
Molecular Weight: 1181.39
Elemental Analysis: C, 55.92; H, 6.48; N, 11.86; O, 20.31; S, 5.43


Related CAS #: 79517-01-4 (acetate); 83150-76-9 (free base);  

Synonym: Longastatin; Sandostatin; Longastatina; Samilstin; Sandostatina; Sandostatine; SMS 201995

IUPAC/Chemical Name: 1-((4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-19-((R)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-benzyl-4-(((2R,3R)-1,3-dihydroxybutan-2-yl)carbamoyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-7-yl)ethyl acetate diacetate

InChi Key: CJLDPLUHCXLWRE-ZMGWVPGSSA-N

InChi Code: InChI=1S/C51H68N10O11S2.2C2H4O2/c1-29(63)41(26-62)58-50(70)43-28-74-73-27-42(59-45(65)36(53)22-32-14-6-4-7-15-32)49(69)56-39(23-33-16-8-5-9-17-33)47(67)57-40(24-34-25-54-37-19-11-10-18-35(34)37)48(68)55-38(20-12-13-21-52)46(66)61-44(51(71)60-43)30(2)72-31(3)64;2*1-2(3)4/h4-11,14-19,25,29-30,36,38-44,54,62-63H,12-13,20-24,26-28,52-53H2,1-3H3,(H,55,68)(H,56,69)(H,57,67)(H,58,70)(H,59,65)(H,60,71)(H,61,66);2*1H3,(H,3,4)/t29-,30?,36-,38+,39+,40-,41-,42+,43+,44+;;/m1../s1

SMILES Code: O=C(N[C@H](CO)[C@@H](C)O)[C@H](CSSC[C@@H]1NC([C@@H](CC2=CC=CC=C2)N)=O)NC([C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC1=O)CC3=CC=CC=C3)=O)CC4=CNC5=C4C=CC=C5)=O)CCCCN)=O)C(C)OC(C)=O)=O.CC(O)=O.CC(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

 
DRUG DESCRIPTION
Sandostatin® (octreotide acetate) Injection, a cyclic octapeptide prepared as a clear sterile solution of octreotide, acetate salt, in a buffered lactic acid solution for administration by deep subcutaneous (intrafat) or intravenous injection. Octreotide acetate, known chemically as L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-Lthreonyl-N-[2-hydroxy-1-(hydroxymethyl)propyl]-, cyclic (2→7)-disulfide; [R-(R*, R*)] acetate salt, is a long-acting octapeptide with pharmacologic actions mimicking those of the natural hormone somatostatin. Sandostatin Injection is available as: sterile 1-mL ampuls in 3 strengths, containing 50, 100, or 500 mcg octreotide (as acetate), and sterile 5-mL multi-dose vials in 2 strengths, containing 200 and 1000 mcg/mL of octreotide (as acetate).
 
Lactic acid and sodium bicarbonate are added to provide a buffered solution, pH to 4.2 ±0.3.  The molecular weight of octreotide acetate is 1019.3 (free peptide, C49H66N10O10S2)
 
CLINICAL PHARMACOLOGY
Sandostatin® (octreotide acetate) exerts pharmacologic actions similar to the natural hormone, somatostatin. It is an even more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Like somatostatin, it also suppresses LH response to GnRH, decreases splanchnic blood flow, and inhibits release of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide. By virtue of these pharmacological actions, Sandostatin has been used to treat the symptoms associated with metastatic carcinoid tumors (flushing and diarrhea), and Vasoactive Intestinal Peptide (VIP) secreting adenomas (watery diarrhea). Sandostatin substantially reduces growth hormone and/or IGF-I (somatomedin C) levels in patients with acromegaly. Single doses of Sandostatin have been shown to inhibit gallbladder contractility and to decrease bile secretion in normal volunteers. In controlled clinical trials the incidence of gallstone or biliary sludge formation was markedly increased (see WARNINGS). Sandostatin suppresses secretion of thyroid stimulating hormone (TSH).
 
 


References

 1: Seymour N, Sawh SC. Mega-dose intravenous octreotide for the treatment of carcinoid crisis: a systematic review. Can J Anaesth. 2013 May;60(5):492-9. doi: 10.1007/s12630-012-9879-1. Epub 2013 Jan 18. Review. PubMed PMID: 23328959.

2: Glatstein M, Scolnik D, Bentur Y. Octreotide for the treatment of sulfonylurea poisoning. Clin Toxicol (Phila). 2012 Nov;50(9):795-804. doi: 10.3109/15563650.2012.734626. Epub 2012 Oct 10. Review. PubMed PMID: 23046209.

3: Shin JK, Jung YH, Bae MN, Baek IW, Kim KJ, Cho CS. Successful treatment of protein-losing enteropathy due to AA amyloidosis with octreotide in a patient with rheumatoid arthritis. Mod Rheumatol. 2013 Mar;23(2):406-11. doi: 10.1007/s10165-012-0675-0. Epub 2012 Jul 20. Review. PubMed PMID: 22815005.

4: Cozzi R, Attanasio R. Octreotide long-acting repeatable for acromegaly. Expert Rev Clin Pharmacol. 2012 Mar;5(2):125-43. doi: 10.1586/ecp.12.4. Review. PubMed PMID: 22390555.

5: Bomanji JB, Papathanasiou ND. ¹¹¹In-DTPA⁰-octreotide (Octreoscan), ¹³¹I-MIBG and other agents for radionuclide therapy of NETs. Eur J Nucl Med Mol Imaging. 2012 Feb;39 Suppl 1:S113-25. doi: 10.1007/s00259-011-2013-8. Review. PubMed PMID: 22388626.

6: Mercadante S, Porzio G. Octreotide for malignant bowel obstruction: twenty years after. Crit Rev Oncol Hematol. 2012 Sep;83(3):388-92. doi: 10.1016/j.critrevonc.2011.12.006. Epub 2012 Jan 25. Review. PubMed PMID: 22277783.

7: Yildirim AE, Altun R, Can S, Ocal S, Akbaş E, Korkmaz M, Selçuk H, Yilmaz U. Idiopathic chylous ascites treated with total parenteral nutrition and octreotide. A case report and review of the literature. Eur J Gastroenterol Hepatol. 2011 Oct;23(10):961-3. doi: 10.1097/MEG.0b013e328349aa2d. Review. PubMed PMID: 21817913.

8: Murphy E, Prommer EE, Mihalyo M, Wilcock A. Octreotide. J Pain Symptom Manage. 2010 Jul;40(1):142-8. Review. PubMed PMID: 21634046.

9: Li J, Wang R, Tang C. Somatostatin and octreotide on the treatment of acute pancreatitis - basic and clinical studies for three decades. Curr Pharm Des. 2011;17(16):1594-601. Review. PubMed PMID: 21548873.

10: Varas-Lorenzo MJ. Long-standing malignant pancreatic carcinoid treated with octreotide. Rev Esp Enferm Dig. 2010 Nov;102(11):662-6. Review. PubMed PMID: 21142389.